1919 Jack Dempsey vs 1988 Mike Tyson

Tyson KO1

 

Dempsey was a great figure in the roaring 20s a legend but a very different era from Tyson’s. Mikes on a different level. I’m afraid it would be explosive and short.

 

Can't give Jack this unfortunately.
Tyson by KO

 

If I was to put money on it, I'd go with that exact result

 

88 Tyson makes short work of Dempsey--KO or stoppage within 3 rounds.

 

Dempsey's manager would definitely hold "the line" for Jack here in not letting him take on such a matchup.

 

Dempsey sends Tyson through the ropes early, but I mean Tyson would be getting out of the ring early because of how quick he stops Dempsey.

 

Jack Dempsey for me. He had great recuperative powers as admitted by Gene Tunney. Tyson never won a fight after hitting the canvas.

 

Dempsey was a great boxer and a great fighter, but... there's nothing for Mike. There's a huge difference in skill and physical preparation. Dempsey was very explosive, but not as explosive as Tyson. He wasn't as strong, didn't punch harder, and was much weaker defensively. I think if he had lasted two rounds, he would have been successful.

Tyson KO maxed out by the third round.

 

Mike would have went through him in a round or two.

 

I like Jack Dempsey. He has become somewhat underrated compared to how he was regarded when I started following boxing.
That being said I think he probably gets taken out pretty quickly. Maybe I am wrong but I see him going right at Tyson, to his detriment. Probably keeps getting knocked down, and fight gets stopped within a few rounds. Tyson was too quick and too powerful at that point, a bad stylistic matchup. Also Tyson is just a better fighter in just about all aspects.